New isomers of 4,1-benzothiazepines.: The first evidence for the desmotropy of seven-membered heterocycles

被引：22

作者：

Csomos, Peter

Fodor, Lajos

Sinkkonen, Jari

Pihlaja, Kalevi

Bernath, Gabor

机构：

[1] Univ Szeged, Inst Pharmaceut Chem, H-6701 Szeged, Hungary

[2] Hungarian Acad Sci, Res Grp Heterocycl Chem, H-6701 Szeged, Hungary

[3] Cty Hosp, Cent Lab, H-5701 Gyuia, Hungary

[4] Univ Turku, Dept Chem, FIN-20014 Turku, Finland

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 32期

基金：

匈牙利科学研究基金会;

关键词：

desmotropy; 4,1-benzothiazepine; beta-lactam; ring transformation;

D O I：

10.1016/j.tetlet.2006.06.018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel procedure was developed for the preparation of 2,3-disubstituted 4, 1 -benzothiazepines, via the ring transformation of (2R*,2aS*)-2-chloro-2a-phenyl-2,2a-dihydro-2H,4H-azeto[1,2-a][3,1]benzothiazin-1-one (1) with sodium etboxide in ethanol. The tautomeric products (R*)-3-ethoxycarbonyl-2-phenyl-3,5-dihydro-4,1-benzothiazepine (4) and 3-ethoxycarbonyl-2-phenyl-1,5dihydro-4,1-benzothiazepine (5) exhibit the rare phenomenon of desmotropy of the condensed seven-membered heterocycles. Surprisingly, these desmotropes could be separated by column chromatography. The products are unexpectedly stable in solution and their structures were proved by means of NMR and mass spectrometry. (c) 2006 Elsevier Ltd. All rights reserved.

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收藏

页码：5665 / 5667

页数：3

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